Wailea rentals with pool

You can select from 1,366 vacation rentals with a pool in Wailea. Whether you’re thinking of staying in Halama Street or another popular neighborhood, we’ll help you find an ideal poolside escape where you can enjoy a dip when you like.

It doesn’t get much better than a vacation rental with a pool, and it doesn’t have to cost a lot with Vrbo. While a range of things will determine how much you’ll pay for your Wailea escape, our filters will help you find an amazing deal. Set your budget and take advantage of our “Discounts” filter to look for properties that offer savings if you stay longer. With an enticing pool at your disposal, you’ll probably want to stick around longer anyway!

August is when the majority of Vrbo guests book a vacation rental with a pool in Wailea, which is in Kihei. On average, temperatures range from 25ºC (77ºF) to 27ºC (81ºF) during this month.

Relaxing comes easy at Vrbo’s vacation rentals with a pool in Wailea. Splash around in the water or simply marvel at the vistas. Tailor your search by “Recommended” or “Guest rating” to find exceptional properties where you can lose yourself in the incredible scenery as your worries float away.

From poolside gatherings to midnight swims under the stars, a vacation rental with a private pool offers plenty of possibilities for relaxation and fun. If you’re traveling to Wailea, use our “Private pool” filter to find accommodations that come with this premium perk.

Wailea Beach, Maui Ocean Center and Kamaole Beach Park are top-rated attractions that’ll keep the whole crew entertained in Wailea. There’s nothing like a fun getaway to bring everyone together, so check out our vacation home rentals in this exciting destination.

When you book a vacation rental with a pool with Vrbo, you’ll enjoy more than the typical hotel experience — think a private space with a place to relax by the water. You’re also covered by our Book with Confidence Guarantee. This means we’re here to guarantee a stress-free stay throughout your entire getaway. Have an unexpected change to the itinerary? Check out our cancellation policies to find out if you are eligible for a complete refund.